It's October

Photo Courtesy
Jessie Hart

October has arrived and it is time to celebrate my former favorite holiday Halloween. During the month, as promised (or threatened) I will spotlight several special evenings I spent on Halloween exploring if my feminine self could actually have a life in the public's eye.

Before I start the experiences, it is important to note several key feelings or happenings. As it turned out the yearly experiences started to vary with the number of times I tried getting out of my gender closet.

An example comes from my first big Halloween adventure, a party when I was in the Army in Germany. As the evening approached the mixture of trepidation along with elation was almost too much to bear. The closer Halloween got, it seemed it was difficult to keep my mind on anything else. 

The problem I had with Halloween was it only came once a year and I would have to wait another whole year to break out of my closet. The pressure affected how much fun I could have.  As I began to have more and more Halloweens under my panty hose, I began to be able to separate which party might be more fun and for what reason. Another example came the night I dressed very glitzy for a bunch of friends and ended up feeling very shunned by my male friends all night long. It turned out the whole process would be a look in how my future would turn out once I began to transition into a full time transgender woman.

It turned out, my favorite Halloween adventures occurred around and with people I didn't know. Probably because I went into the evening with radically different objectives. When I was with friends, primarily I was just fishing for compliments about how good I looked. When I was with strangers, it gave me a chance to see if I could truly present as a woman in public. Once I learned the lesson, I radically changed the way I chose what I was going to wear. I toned down the glitz and tried to turn up the reality and be mistaken for a cis woman, nicely dressed.

There were in between parties I became caught up in which I will explain along the way. One of which when I just happened to glitz my costume up and became part of group of tall women doing the same thing.

Of course October means so much more this year other than Halloween. I have my 73rd birthday coming up soon as well as my wedding, so there is plenty to look forward to. Regardless, even though I don't do any Halloween patties anymore, the holiday will always be special to me as the one day a year I could try life out of my gender closet.  

Going Back?

Photo Courtesy 
Jessie Hart

 Every now and then I read a post about some transgender person who is considering reversing courses and going back to their original gender. Often I think how easy it would be to do just that. Then I realize how I could never de-transition myself. For several reasons.

One of which and perhaps the most important is the fact once I arrived at my goal of being a full time out transgender woman, I felt so natural. In other words, for the first time in my life, my internal feminine soul was able to be freed from its dark closet and take over my former masculine exterior. This all led to me never wanting to give up and return to my previous life as a white privileged male. 

The struggle however was real. I was deeply involved in my sometimes toxic male existence. It involved stages of growth as I learned the true meaning of what I was attempting to do. It was an all encompassing path I found myself on as I traveled a route to be a transgender woman. 

Regardless, I understand others who struggle with the urge to go back to the safe gender life they led before. Many had to battle unaccepting family and friends and made the decision so much more difficult. Even still, easy is not the best course in many cases. Especially when it comes to deciding who your authentic self is then trying to live the life you were always meant to live.

When I think of all the moments in my life when I was trying so hard to find my true gender self, I wish I could have the chance to reclaim just a portion of the time and energy I spent. I took it so far with my nasty mood swings when I couldn't cross dress myself to relief, I nearly lost jobs. . Even further, was the guilt I felt when I was essentially cheating on my wife with another person who turned out to be myself. All of the transgender ripping and tearing I was feeling led me to many self destructive experiences and eventually a suicide attempt. Sadly she (my wife) passed away before we could come up with the final solution to my gender issues. She held her line at never wanting to live with another woman. On the other hand, I went through my only attempt ever to seriously de-transition. I went as far as to grow a beard. Naturally I was miserable.

From the moment she passed on I knew I was free to live my life as I pleased, in whatever gender I chose. Once I did, soon I flourished as my authentic feminine self. 

From that point forward I knew I had found my true gender home, the one deep down I was always knew I was meant to live. From then on, I knew I was never going back to my cross dressing male self. I went as far as I could with hormone replacement therapy to help femininize what the public saw. The HRT really worked with external as well as internal changes such as emotions. I cried more in the first six months as the result of sadness and happiness than I had in my entire life. 

I especially don't understand how a transgender person who has gone as far as HRT could ever go back to another gender universe but in a world where anything can happen I'm sure I will read about someone de-transitioning again. The current anti LGBTQ atmosphere in more than a few area's doesn't help those who want to gender transition into their authentic selves. It's a difficult path to follow.  

The Basics

Yesterday, I wrote a post concerning using the basics of using the women's room. Of course, as you transition genders from male to female or female to male, there are giant gender stereotypes you have to conquer. 

Examples are many, such as cis women have this sacred place to go (literally) when they use the restroom. Another would be women don't follow sports or drink beer as much as their male counterparts. Along the way I was able to put those stereotypes behind me as my cis when friends were every ounce the fan I was and could drink me under the table. 

If you look around at other women, they are as diverse as the rainbow some of them reject. The only major impact in society I see from women as a whole is they have moved away from dressing up as much as they used to. A disappointment to many cross dressers and or novice transgender women as they journey from their closets only to find in order to blend into the feminine population as a whole they had to change the idea of what they were wearing. Unless they were prepared to face added scrutiny. 

Other novice transgender women of a later age had to face the fact they were not a teenaged girl when they transitioned and no matter what couldn't dress like one. I fell into that trap and turned many A-Ha moments into Connie's Ha-Ha moments when I was laughed out of places I should have been accepted in. When the laughing stopped, I went back to my transgender drawing board, hitched up my big girl panties and went back in. Deep down I knew to be successful in my goal of presenting as a woman was going to take more work than I thought. 

I wonder now what I was thinking as I began to build a brand new person as my authentic feminine self. After all, she had waited years to get out of the dark and live. I don't think I grasped in the moment what I was asking. Perhaps I was too immersed in shedding the remnants of my old male life. Whatever the case, I don't believe I was totally ready for what happened to me.  One example is how suddenly I was able to find women who accepted me. I looked for and received more attention as a transgender woman than I ever did as a man. Maybe because the women sensed I had given up on the perceived masculine toxicity I had to live with.

The biggest challenge was building a good person others could relate to and I could interact with, learn from and develop as the woman I always knew I had been. At that point, the basics revolved around how I communicated with the new world I was facing. I couldn't believe the gender euphoria I felt when I began to communicate one on one with other women. 

As it turned out, the period of gender adjustment was not so different to the adjustments I had to make when I went through Army infantry basic training so many years before. Both transitions were intense and required an incredible amount of work to accomplish. Of course the gender basic was much more pleasurable than the Army one and I gained an incredible amount of respect for my new self. 

Restroom Etiquette

Early women's room photo
Jessie Hart

Every now and then I feel the need to share my learning time using the women's restroom. 

Even though I had exactly no experience of using the "room" as a novice transgender woman, I had plenty of experience with women being totally inappropriate when using the women's room. I can't tell you how many times I cleaned up messes, tried to repair broken stalls and even had to remove feminine hygiene products from toilets. All of this occurred when I was a restaurant manager so you can probably imagine the problems I encountered.

So before I even started to have to use the "room" on my way to playing in the girl's sandbox, a couple of preconceived ideas I had about others (women) who used it were destroyed. Women were definitely not always the cleaner or well behaved gender when it came to rest room usage. An example was how quickly I learned to check the toilet seat before I sat down.

Many other "rules" were self explanatory such as sitting down when you pee. Other not so evident rules include trying to direct your pee stream into the bowl to mimic the sound a cis woman makes in the next stall over. I even went as far as carrying a tampon or pad in my purse if I was asked to provide one by another woman. 

Truthfully the one thing I had to get used to was being greeted eye to eye in the rest room by other women. Of course I was so used to the exact opposite in macho men's rooms I sued to frequent. Early on I became used to it and often tried to speak first. 

Another hard and fast rule I couldn't forget (no matter how quickly I was trying to finish and leave) was to always, always, always stop to wash my hands which was a great time to check my makeup and hair. Another surprise was I rarely heard any of the super secret conversations I thought women were supposed to have when they head off together to use the restroom. So called girl talk became boring quickly. 

Even though it has been years since I have been challenged about using the rest room of my choice, back in the day when I was first coming out of my gender closet that wasn't the case. One night I had the police called on me for just having to pee, all the way to some cis woman calling me a pervert. To this day I still carry the scars of those long ago encounters, 

I am sure you all may have your own restroom etiquette experiences such as never putting your purse on the floor. Plus some of you are lucky enough to live in a state where it is legal to use the restroom of your choice. Sadly we have to go through all of this to do what should come naturally. You shouldn't have to hold it in all day just because narrow gender minded people still exist. Just don't forget to follow a few simple rules in the room to help yourself along.     

Taking the Gamble

Photo Courtesy
Jessie Hart

 I have never been good at or desired to be good at any form of gambling. However taking a gamble was completely the case when I decided to play my gender cards and transition into a transgender woman. 

Since it took me nearly a half a century of being a very serious cross dresser, I had plenty of time to consider my next move before I made it. Over the past, I have given more than a few examples of my many failures attempting to break out of my gender closet, as well as successes also. One of my examples of success was the night I was by myself in Columbus, Ohio attending a party at a transgender friends house. For whatever unknown (now) reason, I decided to go all in black. I wore a pair of shorts which were not short with black tights, flats and a black sweater. A dark wig completed my outfit. I looked at myself in the mirror and decided my looks were attractive enough without going overboard and out the door I went.

Once I arrived at the party, I found everyone on the patio because it still was a warmish fall evening and found I had dressed appropriately for the evening. After awhile, a single woman approached me who I presumed to be a lesbian. Our conversation moved along smoothly until we decided to leave for awhile and go to a well known large lesbian venue in the nearby downtown area. I gambled and said yes since I knew my way around Columbus and could return if I needed to. Later on in the evening, we went on our separate ways and I never saw her at any other parties.

Another time I gambled in the opposite direction and didn't go/stay with a guy in a bar in Cleveland, It happened after I submitted myself to a professional makeover and couldn't believe the change, It was so dramatic I was invited to tag along with the transvestite groups "A-Listers" or the self perceived prettiest cross dressers. They were shocked when a man approached me to stay and play pin ball with him. I was flattered but told him no because I didn't know if he knew the gender truth about me and if something negative happened, I didn't know the way back to the hotel where we were staying. I left forever wondering what would have happened if I gambled and stayed. 

Overall, the biggest gamble I ever took was when I came out as a transvestite to a few close friends in the army. This was way back before the so called more liberal LGBTQ "Don't ask Don't tell" days in the military. I worked in a very public job as a radio disc jockey position in Stuttgart, Germany. I could have lost it as well as being dishonorably discharged if the wrong people found out. Which they never did. I went on to marry one of the friends I came out to and she is the mother of my beloved supportive daughter. My gamble really paid off.

These are just a few of the gambles I took in my life. I do believe if you don't take some gambles you won't get ahead in your life. Plus just living pushes you into taking gambles. Regardless, I always tried to play my cards the best way I could. 

Pushing too Hard

Jean Skirt Look
Back in the day

Over the many years I spent trying to find my way into a feminine world, often I was guilty of pushing too hard. A primary example was when for once I was able to put my cross dressing act all together. In other words I was able to walk without falling in sidewalk cracks plus I felt my makeup, outfit and hair all looked as good as possible. I felt good and the whole experience was a positive one. 

The next time I went out I thought I would build on the last experience but didn't quite do it. In those days I was still validating my life as a cross dresser or transvestite by what men thought of me. It wasn't until much later when I learned it was so much more important to me to be judged and validated by other women around me. So, to make a long story short, I went overboard in my dress, makeup and especially hair. The end result was similar to a matador waving a red cape at a bull. I stood out like a sore thumb wherever I went. In addition, many times I was thrown back to square one and had to start all over with how I dressed myself. 

It took awhile of tough loving my feminine self but I finally learned all my trashy outfits and crazy wigs weren't working, I finally settled into a more or less everyday persona of who I would eventually become on an everyday basis. I substituted too short and tight mini skirts for more proper yet flattering jean skirts and I used flowing fun blouses/tops to help disguise my all too hated male figure. In essence I ended up killing two birds with one stone. My appearance was still on the cutting edge of having fun without going so far I was attracting unwanted attention.

Also around that time was when I quit pushing so hard and began to relax on most fronts. Now I could pay more attention in rounding out more of my total self. The way I moved, the way I talked began to come together, From then on pushing harder was out and a new confidence was in. I even settled on the same wig which I nearly wore out. 

Through it all though I don't want to give the idea that anything was a pushover when it came to my gender transition. It was just like I could start on starting on settling more of the more mundane problems I was experiencing. One of which was not so mundane was using the women's restroom which is a topic I revisit fairly often in my posts. It is no secret I like to drink beer and beer doesn't stay with you long so I had to use the women's room frequently. Often it was the ultimate answer to how I was presenting as a transgender woman. I found in many venues other patrons would draw the line and complain if I needed to pee. Having the cops called on me was a decidedly unpleasant experience

Another small thing I did to try to normalize being a single woman in a hetero bar was to use my cell phone as a prop. I would sit down, order and act like I was texting someone else to join me. As you can tell I was trying every little thing I could to make it in feminine world and earn my right to play in the girl's sandbox.

When I quit pushing so hard, the easier it became. 
      

Girls Night Out

Girls Night Out #1 
I am on the left.

As I was first attempting to survive in the feminine world without the "Ha-Ha" moments Connie mentioned in a recent comment on my :Ah-Ha" post, I craved any opportunity I had to join a women's night out. In a relatively short period of time I was fortunate and was invited to four, One of which was even a bachelorette party which sadly was cancelled. Two of the remaining invites were with a group of cis women friends I became close to until similar to many women they got married and moved away from the group. Children were involved also.

Perhaps the most exciting was my first invite because I had no idea of what to expect seeing as how there were going to be a couple other women attending who I didn't know. How would they accept a transgender woman? The answer was one didn't seem to care and the other rejected me quickly.  

My first issue was what to wear of course. I wanted to appear as attractive as I could without over-dressing the other women. As you can see in the picture, I think I achieved the desired effect. My second issue was what would the conversation be when no men were present and again how would I fit in. The whole process (per norm) turned out to be just a whole lot of worry about nothing. Most of the conversation dealt with family and children so I just inserted my daughter's examples when I could. During the space of the evening I even forgot to worry about my voice. Everything must have worked out fine because shortly after the first night out, I was invited to another before I moved away with Liz to Cincinnati.

Perhaps the most surprising girl's night out occurred when I was invited by a group of servers from one of the venues I was going to on a regular basis to join them for a get together at another trendy venue. I was terrified when I said yes. How would I react to going with a group of younger, more attractive women to a venue I had only been to a couple of times. This time there wasn't much conversation because of the amount of guys the rest of the group attracted. It turned out to be like I was almost invisible as the night went on. Lesson learned.

As far as other lessons learned, I discovered no new earth shattering gender secrets when women gather.  Naturally, it was no big surprise when the younger women I was with got their flirt on with men and forgot about the group all together. Even though all of that happened I was pleased I survived the evening without doing anything gender ignorant.

Overall, all of the girls nights out I was invited to were fun and learning experiences. I was happy to accept the invitation. 

  

A-Ha Moments

Beaded Trans Hair Piece by
Liz T Designs 

 This is an extension of several recent posts I have written about  my gender transition but few of them were about a-ha moments along the way. I guess you could call them rare moments of gender euphoria before I ever thought of such a phrase which I of course didn't invent. 

The first a-ha moment I had was early in life when I realized dressing up as a girl wasn't enough. Being a girl was the best idea. There was no way I could know this was the first indication I was transgender and not a cross dresser. 

Fast forward several years of gender struggle, my next moments of gender euphoria could all be wrapped up in all the Halloween parties I went to. Through them all I learned the power of dressing as a woman was real and I loved it all. Especially the parties when I was mistaken for a well dressed woman not in costume. More on those parties when I spotlight Halloween in my October posts.

In essence Halloween taught me there was a chance I could pursue farther the idea of living my life in a feminine world and survive. 

Finally Halloween became just another day for me and I moved on to other a-ha moments came when I decided male dominated gay venues weren't working for me. I became quite frustrated when I was treated like a drag queen or when I was completely discriminated against for simply being myself. When I learned I could frequent large sports bars or the occasional small lesbian bar and be much happier.  Often I learned the hard way I could live in the world and play in the girls sandbox. The more I did it, the more I wanted to do to expand my knowledge of being an out transgender woman. Which in itself was a true revelation.

About this time a-ha moments came fast and furious as I learned the hard way how to exist and communicate with other women. For the second time in my life woman's fashion took a back seat to more important functions such as establishing myself as a brand new feminine person. All of the sudden I was completely immersed with communicating with the world as a transgender woman.

Perhaps the biggest a-ha moment in my transgender life came when I started hormone replacement therapy. For once I was syncing up the inner woman who I strongly felt needed to live with my external testosterone poisoned exterior self. In a short period of time, my breasts and hair grew wonderfully along with a softening of my skin and features. Perhaps most surprisingly were the changes to my emotions. I became decidedly less aggressive when dealing with world. I guess you could say HRT softened my world.

Of course there are many other a-ha moments which may come along in your life such as passing a mirror and noticing a woman looking back at you. Hopefully your positive moments out number your negative ones.  

Living the Dream

 

Photo Courtesy
Jessie Hart

For so many years I lived with what I thought was the impossible dream. That dream of course was wondering if I could ever live a life as a full time transgender woman. Although for the longest time I didn't see how I was ever going to make it to my goal, slowly but surely I kept moving towards it. 

I like to say I was a serious cross dresser for fifty years of my life. During the half century I made a few strides in makeup and fashion only to find myself headed back to the cross dressing drawing board time and time again. The only positive aspect of the experiences were I tried to learn from each one. What worked and what didn't. Every positive gave me hope for the future. 

Along the way I have written concerning the gender maze I found myself in. I felt everytime I achieved one goal and turned the corner, I found another corner to deal with. Almost all with no positive intervention from any other person. Even though my wives knew of my cross dressing activities, they were rarely participants. And, if the truth be known, many times I didn't want to follow the ideas of what a woman meant to them. Even to the point of trying my best to dress to blend when and if we ever went out together as girlfriends. Examples were when my second wife and I used to journey to Columbus, Ohio to eat at a LGBT friendly restaurant. It got the point of me wearing jeans and a sweater and she (my wife) still didn't like the way I looked. Deep down I knew I was struggling to find my feminine identity and I stayed on course with what I wanted to wear. 

Slowly but so uncertainly my small successes added up and my dream of living full time became more than a distant reality. After the fewer and fewer setbacks I had, I righted the gender ship and realized yet again how natural my feminine side felt. When I went out as a novice transgender woman I felt the world was in the right place and I even went as far as feeling out of place when I went out as a guy. 

Finally even I could not deny it any longer, I was meant to live as a transgender woman. I started hormone replacement therapy and started to transition my exterior as close as I could to match my feminine soul. It all worked so well and I was left no alternative to living my dream. The hormones fueled the fire which burnt my final bridge back to any male life I had left. 

After I made the commitment to giving away all of my male clothes, a new voice inside of me was asking what took so long. My only answer was I was stubborn and wanted to hang on to whatever white male privilege as long as I could. Most certainly giving it all up was one of the best decisions I ever made.

My biggest lesson from my lifetime of experience is, not trying at all is the biggest disaster.